Uncle Chuck's Vacation

My uncle Chuck is a nice man and my best friend. We have always been close and he's not like other men. He is always gentle with me in the things that matter to us. For my twelfth birthday he told me that he wanted to take me on a long trip. He asked my parents if he could take me on this trip after school let out for the Summer, they gave him permission. I was excited and I could hardly wait for the three months to go by and for uncle Chuck to come pick me up.

The day came and we loaded my suitcases into his car and headed out for his house. As we went along, he asked if I would promise to keep secret what we did alone. He told me that I could talk about the trip but nothing else. I promised and he patted my hand. When we arrived at his place he asked me if I wanted a glass of JD and coke and of course I did, what young boy would miss a chance to try some. He said that he had special movies he wanted to share with me. We settled in on the sofa next to each other and watched the first movie about two women making love. My little cock twitched with excitement and after the first movie he fixed us an other drink only mine was smaller this time.

Before the next movie started he asked me if I wanted to sit on his lap like I did at the fireworks in the park. I nodded yes remembering that experience. The show had started and it became dark where we were seated and he had me sit on his lap with my legs dangling on each side of him. It wasn't long before I felt a hardness between the cheeks of my tiny ass. Every time I jumped at a display, he would bring me down on that hardness and hold me there. I liked the feeling of his hard and I would wiggle slowly, so I was eager to hop on. The movie was about some young boys dressing in girls clothing. I was glued to the screen and hadn't noticed that uncle Chuck had gotten my tiny cock out of my shorts.

To make a long story short, he challenged me to dress like them and I did. He made me his sex goddess for the trip and made sure I had everything I needed to become his girl. I inherited his ranch and money and still dress today as the queen of the land.


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  • I loved that story. So similar to mine. I was 14 and my dads 2 mates(gay) about 45 owned a shop. I would always ask for a ciggy and hang out in there. It started with one of them telling me i had something on my shirt. He was holding the botyom of my tshirt and wipinv something off. I could blatanly feel his fingers flicking and touching my cock. Anyway this went in for about 6 weeks untill im not sure what happened but we ended up in the back of the shop all masturbating. They ended up splitting up and it got messy. But i kept going to see one of them. It ended up with me going up to his place and watching porn whilst he sucked me off. None of my friends knew and it was our secret. I actually started getting feelings for this guy but he kept telling me im not gay. I used to go to his house. Have a couple of vodkas and go through to the bedroom.lie on the bed naked and sniff poppers. He qould come in and suck me off. One day doing this, he pulled out ky jelly and told me.to lie.on my belly. He smeared a load on my tight virgin hole and fucked me. I loved the idea that i was one of the slags off the estate being filthy. I.always.imagined myself as a girl when i got fucked. Anyway they got back togetherbabout a year later and i was now a plaything for 2 men..i ended up running away from home and.living there for 2 years. I was regularly fuckes by other men they brought back to the house and made to get in the middle. I loved it. This was 20 years ago and i still fantasise about being abused by a group of old white men or groups of black men. Im in a straight relationship and have always wanted more. Reply if you can help or just tell me what you think.

  • When I was growing up the old grandpa type man that lived behind us would fix my bike all the time and show me how to maintain things. One day he asked me if I would show him my penis and for some reason I did not think it was a big deal so I did it. He was sitting down on one of those stools with wheels on it and he reached right out as soon as my pants were down and started stroking it. Minutes later he was sucking on me and telling me the whole time how much he appreciated this stay between just us, man it sure felt good so I told no one at all about it.

  • So did this go on for a long time and did you ever do him?

  • Yes and I used to go to his place wearing my sisters clothes, he liked that and would take me up to his bedroom, take all his clothes off and lie on the bed with me. it made me feel so horny in my nylon knickers and my school blouse. We would suck each other, kiss and fondle until one day I let him turn me over, gel my arse and he pushed that big stiffy inside. It was wonderful feeling his dick in me with his hand stroking my dick through my knickers and then feeling his dick swell as his cum pumped into me and me wetting the knickers as I stot my load as well.

  • Ummm yes I too enjoyed Pinky's cock inside me. Pinky is what I called Uncle Chuck be cause his cock head always looked pink to me. I called him that when we were alone or whenever no one was in ear-shot of us. I have never forgotten the first time he slipped it into me. He was so gentle as each time he went in and deeper each time. Oh and when he finally had it all in, it was such a beautiful feeling. I loved dressing for him.

  • Uncle Chuck is a sick bastard

  • I am gay and also lost virginity to uncle, while my mom and aunt watched.

  • What?

  • The family that fucks together raises " Uncle Chucks " together.

  • You could say that but it's not always true.

  • So, your "long trip" was really a molestation vacation. I guess you told your parents that you got to be the cowgirl of your dreams.

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